Title:
METHOD FOR PRODUCING OPTICALLY ACTIVE 1-AMINO-2-VINYLCYCLOPROPANECARBOXYLIC ACID ESTER
Document Type and Number:
WIPO Patent Application WO/2011/019066
Kind Code:
A1
Abstract:
An optically active 1-amino-2-vinylcyclopropanecarboxylic acid ester represented by formula (4), which is useful as an intermediate in synthesizing a medicine, can be produced by a method comprising a step for subjecting an optically active 1-N-(arylmethylene)amino-2-vinylcyclopropanecarboxylic acid ester represented by formula (3), which is obtained by reacting an N-(arylmethylene)glycine ester represented by formula (1) with a compound represented by formula (2) in the presence of a base and an optically active quaternary ammonium salt, to imine hydrolysis.
Inventors:
AIKAWA TOSHIAKI (JP)
YASUOKA JUNICHI (JP)
IKEMOTO TETSUYA (JP)
YASUOKA JUNICHI (JP)
IKEMOTO TETSUYA (JP)
Application Number:
PCT/JP2010/063674
Publication Date:
February 17, 2011
Filing Date:
August 05, 2010
Export Citation:
Assignee:
SUMITOMO CHEMICAL CO (JP)
AIKAWA TOSHIAKI (JP)
YASUOKA JUNICHI (JP)
IKEMOTO TETSUYA (JP)
AIKAWA TOSHIAKI (JP)
YASUOKA JUNICHI (JP)
IKEMOTO TETSUYA (JP)
International Classes:
C07C251/24; C07B53/00; C07B61/00
Foreign References:
| JP2002522554A | 2002-07-23 | |||
| JP2001048866A | 2001-02-20 | |||
| JP2007515405A | 2007-06-14 |
Other References:
BEAULIEU P L; ET AL.: "Synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid vinyl-ACCA derivatives: Key intermediates for the preparation of inhibitors of the hepatitis C virus NS3 protease", JOURNAL OF ORGANIC CHEMISTRY, vol. 70, no. 15, 22 July 2005 (2005-07-22), pages 5869 - 5879, XP002415438
KEVIN M. BELYK, ET AL.: "Enantioselective Synthesis of (1R,2S)-1-Amino-2-vinylcyclopropanecarboxylic Acid Ethyl Ester (Vinyl-ACCA-OEt) by Asymmetric Phase-Transfer Catalyzed Cyclopropanation of (E)-N-Phenylmethyleneglycine Ethyl Ester", ORGANIC PROCESS RESEARCH & DEVELOPMENT, vol. 14, no. 3, 2010, pages 692 - 700, XP008151560
XINGZHONG ZENG, ET AL.: "Epimerization Reaction of a Substituted Vinylcyclopropane Catalyzed by Ruthenium Carbenes: Mechanistic Analysis", JOURNAL OF ORGANIC CHEMISTRY, vol. 71, no. 23, 2006, pages 8864 - 8875, XP008151569
TAKASHI OOI, ET AL.: "Practical Catalytic Enantioselective Synthesis of alpha,alpha-Dialkyl-alpha-amino Acids by Chiral Phase-Transfer Catalysis", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 122, no. 21, 2000, pages 5228 - 5229, XP002941729
JOURNAL OF ORGANIC CHEMISTRY, vol. 70, 2005, pages 5869 - 5879
TETRAHEDRON LETTERS, vol. 40, 1999, pages 8671 - 8674
TETRAHEDRON, vol. 60, 2004, pages 7743 - 7754
JOURNAL OF AMERICAN CHEMICAL SOCIETY, vol. 122, 2000, pages 5228 - 5229
TETRAHEDRON LETTERS, vol. 44, 2003, pages 5629 - 5632
ANGEWANDTE CHEMIE INTERNATIONAL EDITION, vol. 44, 2005, pages 1549 - 1551
KEVIN M. BELYK, ET AL.: "Enantioselective Synthesis of (1R,2S)-1-Amino-2-vinylcyclopropanecarboxylic Acid Ethyl Ester (Vinyl-ACCA-OEt) by Asymmetric Phase-Transfer Catalyzed Cyclopropanation of (E)-N-Phenylmethyleneglycine Ethyl Ester", ORGANIC PROCESS RESEARCH & DEVELOPMENT, vol. 14, no. 3, 2010, pages 692 - 700, XP008151560
XINGZHONG ZENG, ET AL.: "Epimerization Reaction of a Substituted Vinylcyclopropane Catalyzed by Ruthenium Carbenes: Mechanistic Analysis", JOURNAL OF ORGANIC CHEMISTRY, vol. 71, no. 23, 2006, pages 8864 - 8875, XP008151569
TAKASHI OOI, ET AL.: "Practical Catalytic Enantioselective Synthesis of alpha,alpha-Dialkyl-alpha-amino Acids by Chiral Phase-Transfer Catalysis", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 122, no. 21, 2000, pages 5228 - 5229, XP002941729
JOURNAL OF ORGANIC CHEMISTRY, vol. 70, 2005, pages 5869 - 5879
TETRAHEDRON LETTERS, vol. 40, 1999, pages 8671 - 8674
TETRAHEDRON, vol. 60, 2004, pages 7743 - 7754
JOURNAL OF AMERICAN CHEMICAL SOCIETY, vol. 122, 2000, pages 5228 - 5229
TETRAHEDRON LETTERS, vol. 44, 2003, pages 5629 - 5632
ANGEWANDTE CHEMIE INTERNATIONAL EDITION, vol. 44, 2005, pages 1549 - 1551
Attorney, Agent or Firm:
NAKAYAMA, Tohru et al. (JP)
Toru Nakayama (JP)
Toru Nakayama (JP)
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